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q Chemistry and Toxicity of Disinfection Concerns about possible adverse health effects of drinking water dis- infection have centered on chemical by-products produced by reactions of chlorine with various organic precursors during water treatment. The presence of certain organic compounds in raw water prior to treatment can be attributed to chemical manufacturing, processing, distribution, uses, or urban and agricultural land runoff. However, most of the carbon in typical surface waters is found in natural humic materials, which are potential precursors of toxic disinfection by-products (Rook, 1976; Thur- man, 19851. Many recent studies discussed in this chapter have addressed disinfec- tion by-products produced from these aquatic humic materials, which consist of complex natural mixtures of humic and fulvic acids plus neutral and basic components produced mainly by decaying vegetation. CHLORINATION Reactions and By-Products of Chlorination Although chlorination has the desired effect of inactivating pathogenic microorganisms through the disinfecting reactions of chlorine, as well as the additional desired effect of oxidizing many organic molecules to form CO2 (Helz et al., 1980; Jolley et al., 1985), this method of disinfection also produces chlorinated by-products and other incompletely oxidized compounds of potential concern. Noteworthy contributions to the chem- istry of drinking water chlorination over the past few years have included 27

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28 DR'N K'NG WATER AND H EALTH VANILLIC ACID SUBSTITUTION PATTERNS: COOH OCH3 CH2CH2COOH CH=CHCOOH OCH3 OH OH OH ~ OCH3 SYRINGIC ACID SUBSTITUTION PATTERNS: COOH CH2CH2COOH CH=CHCOOH H3CO ~ OCH3 H3CO ~ OCH 3 H3CO ~ OCH3 OH OH OH 3,5-DHBA SUBSTITUTION PATTERNS: COOHOH COOH CH3 OH HO OCR for page 27
Chemistry and Toxicity of Disinfection 29 able levels of chloroform. Resorcinol, as suggested earlier by Rook (1977), consumed a large quantity of chlorine (7 moles per mole of resorcinol) and rapidly produced 1 mole of chloroform. Similar results were produced with their other model compounds, suggesting that chloroform is a primary re- action product of chlorination of aquatic humic materials that contain sub- structures similar to these model compounds. Other by-products produced by their model compounds are shown in Table 3-1. High chlorine-to-carbon ratios favored the production of nonvolatile hydrophilic by-products. Boyce and Hornig (1983) studied chloroform production from chlorination of 1,3-dihydroxyaromatic compounds and simple methyl ketones, which they confirmed to be efficient at producing chloroform. With isotope labeling, they unambiguously demonstrated that the C2 position of resorcinol is re- sponsible for chloroform generation, as previously hypothesized by Rook (1977) and Norwood et al. (19801. Boyce and Hornig (1983) further dem- onstrated that the specific types of chlorinated products depend on both pH and the relative concentrations of chlorine and substrate in solution. The by- products that they obtained from resorcinol at various chlorine concentrations and pH values are shown in Table 3-2 and confirm the previous observations of Norwood et al. (1980) regarding by-products formed at neutral pH. Based on these results and previous hypotheses of Moye (1967) and Rook (1980), Boyce and Hornig proposed a comprehensive mechanism for the conversion of 1,3-dihydroxyaromatic structures to chloroform by aqueous chlorination. A portion of this proposed mechanism, modified and reproduced in Figure 3-2, involves successive electrophilic attack of chlorine to produce substituted resorcinols (I) with the eventual loss of aromatic character to produce the intermediate pentachlororesorcinol (II). This is followed by hydrolytic ring cleavage and a number of other sub- stitution and hydrolysis reactions to produce chloroform and short-chain chlorinated acids, in this case chloromatic acid (VI). De Leer and Erkelens (1985) attempted to support the mechanism pro- posed by Boyce and Hornig (1983) by synthesizing the proposed inter- mediate pentachlororesorcinol according to the method of Zincke (1890) and subjecting it to aqueous chlorination at neutral pH. Although the chlorination of resorcinol and pentachlororesorcinol produced several iden- tical products, large discrepancies were seen in apparent reaction rate, chloroform production, and products, indicating that pentachlororesorcinol is not a major intermediate. De Leer and Erkelens (1985) further concluded that the principal reaction and most important side reaction are C6H6O2 + 7C12 + 4H2O ~ CHC13 + CO2 + cis-HOOCCC1 = CHCOOH + 10HC1, and C6H6O2 ~ cis-HOOCCC1 = CHCH2COOH + CO2 or CHC13, but that many side reactions producing other chloroform precursors and highly oxidized products occur.

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30 DRINKING WATER AND HEALTH TABLE 3-1 Reaction Products from Model Compounds and Hypochlorous Acid (HOCl~a Products Identified Reactant At 0.5 Cl2/C At 2.0 Cl2/C 1,3 DIHYDROXY BENZENE OH OH 'JC1X(X=1-3) HO OH H Cl,4~'C1 1 ~C1 O O CHC13 CHC13 O O 11 11 HO-C-C=3C- C-OH 1 1 H C1 CC13COOH 3-METHOXY-4 HYDROXY CINNAMIC ACID CH=CHCOOH CCH3 OH CH=CHCOOH LOCH OH r3 CH=CHCOOH ~C12 OCH3 OH CH=CHC 1 OCH3 OH CH=CHC 1 OCCIH3 OH CHC 13 CHC13 CHC12COOH CC13COOH aFrom Norwood et al. (1980) with permission.

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31 it: . - c~ - o ~ - o no Hi 1 to - x o . - 'e of o - <5 ~ rat V 0 Ct O so ._ ~ X ._ ~0 Cal =, 1 ~ O o . _ Ct X o I ~ O _Q ~ m x En ~ TIC C ~ O_ ~O Ct~ C) i,, O a O4v X 0 of o ~ / - ~ 0 ~O:V o4o o 4o ~ 0 off C: _ ~_ ~ ~ 0 ~ O 0 et of 04o of o~ C: ~ _ ~ ~ 0 ~ 0 off o~o V _ ~_ C: o ~ o / ~ o~ 0~_ ~ - v

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32 1 _ o _ rT ~0 ._ o ~ ~) ~ ~ 3 o \ / ~ ~ ~ @~5 i ~ ~ ~ ~ G ~ ~3~ on ~ ~_ _ _ ~o o o \ / o ~ ~ _ ~ Ott of o _ _ o o ~ ~ _ Otto . ~ o 5~ rig ~ ~ S 1 0~0 ~ ~ O O O o 0~0 ~ O god o o o o 0~ O O O O o - O O a, o o ~ O O O 11 11 O O O O ^ ^ O O O O O O ^ O O O

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33 ~o - o o o o o o . = o . - o o o .. 11 _ _ o o o o ^ ^ o o o o o o _ _ o o o \/ o o O I[ o o o - ~o ,, ~o o o o o _ _ o o o 8 o o o o ^ o o 3 11 - o o ^ o o o o o ~ X .; o . ~ o . o ~ ~ o :~ ~ .s ~ o 511 ~ ~ E S ~ ~ = ~ ~ ~ C ~ o o _ ~ ~ ~ ~ 5 o - ~ I ~= S Eo ~ ~ = 0 - 0 = ~ ~ ~ &~t o ~ o o ~ O o o E ~ S~ ~ - o o o e- ^ o x - ~ .E ~ o o ~ ^ o

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34 DR! N K'NG WATER AN D H EALTH OH 3 HOC1 OH o 11 C 1 2CH CCC1 =CHCC 1 2CO2H III o 11 C 1 oCCCC 1 =CHCHC! V OH-(H+)+HOC 1 2 -CHC 1 3-20H OH I C 1 lilts, 2 HOC \j~ OH o 0 1 C1~rJ~ I OH-(H+)+H2O H~O: II OC _ C 1 3CCCC 1 =CHCC 1 2CO2H 2 IV HO2CCC 1 =CHCO2H VI FIGURE 3-2 Abbreviation of mechanism proposed by Boyce and Hornig (1983) for the aqueous chlorination of resorcinol (adapted from Norwood, 1985). Thus, it appears from the above studies of model compounds that non- selective aqueous chlorination of activated aromatic ring systems produces not only chloroform (a volatile hydrophobic by-product) but many non- volatile hydrophilic chlorinated aromatic by-products as well. ISOLATED ACIDS Working with isolated aquatic humic and fulvic acids, Christman and co-workers (Christman et al. 1980, 1983, Johnson et al., 1982; Norwood et al., 1983) identified more than 100 different chlorination products by gas chromatographic/mass spectroscopic methods at a 4:1 chlorine-to- carbon mole ratio. Some of these products are shown in Tables 3-1 and 3-2. Chlorination of several humic and fulvic acid samples from the same source produced significant differences in product mixtures. A notable difference was that most products of fulvic acid chlorination contained chlorine, whereas most humic acid samples produced at high pH did not. In both cases, however, the dominant chlorinated products were chloro- form and chlorinated aliphatic acids, especially dichloroacetic acid (DCA), trichloroacetic acid (TCA), chloroform, dichlorosuccinic acid, and di- chloromalonic acid. A variety of short-chain, nonvolatile aliphatic halogenated products (listed by Norwood, 1985) result from the exposure of aquatic humic and fulvic acids to chlorine:

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Chemistry and Toxicity of Disinfection 35 Name Trichloromethane (chloroform) Bromodichloromethane Trichloroethanal (chloral) Chloroethanoic acid (chloroacetic acid) Dichloroethanoic acid (dichloroacetic acid, DCA) Trichloroethanoic acid (trichloroacetic acid, TCA) 2,2-Dichloropropanoic acid 3,3-Dichloropropenoic acid 2,3,3-Trichloropropenoic acid Dichloropropanedioic acid (dichloromalonic acid, DCM) Butanedioic acid (succinic acid) Chlorobutanedioic acid (chlorosuccinic acid) 2,2-Dichlorobutanedioic acid (a,cx-dichlorosuccinic acid, DCS) cis-Chlorobutenedioic acid (chloromaleic acid) cis-Dichlorobutenedioic acid (dichloromaleic acid) trans-Dichlorobutenedioic acid (dichlorofumaric acid) Molecular Formula CHC13 CHBrcl2 CC13CHO H2CClCO2H HCC12CO2H CC13CO2H CH3CC12CO2H CC12 = CHCO2H CC12 = CClCO2H HO2CCC12CO2H HO2C(CH2~2CO2H HO2CCH2CHClCO2H HO2CCC12CH2CO2H HO2CCH = CClCO2H HO2CCC1 = CClCO2H HO2CCC1= CClCO2H The apparent dominance of C2-chlorinated acids is in agreement with the findings of Quimby et al. (1980), who reported the tentative identification of TCA and halogenated phenols after soil extract chlorination, and Rook (1980), who found that DCA and TCA were the principal constituents in methylene chloride extracts of Rotterdam drinking water after breakpoint chlorination. However, no halogenated aromatic products were detected after chlorination of actual aquatic humic and fulvic acids under high pH conditions. A large number of monobasic and dibasic unchlorinated aliphatic acids, from oxalic up to the C27 monobasic fatty acid, were identified from the humic acid fraction (Table 3-3~. Only a few of the dibasic acids were associated with the fulvic acid fraction, and almost none of the monobasic

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36 DRINKING WATER AND HEALTH TABLE 3-3 Non-Chlorine-Containing Products of Aquatic Humic and Fulvic Acidsa Compound Class Number Identifiedb Major Compounds Benzenecarboxylic acid (Carboxyphenyl)- glyoxylic acids Monobasic acids Dibasic acids 16 17 ~ (COoH)n nC= 1-5 COCOOH ~ (COoH)n nd = 2-4 2H3C (CH2)n~OOH ne = 7-25 HOOC-(CH2)n~OOH n = 0-8 aFrom Norwood (1985) with permission. bIncludes only the more confident identifications. CAll possible isomers detected. Several isomers detected in each case; identifications considered very tentative. eNot all n values detected; some may have been below the detection limit. acids were detected. The dibasic aliphatic acids are generally of low molecular weight, containing 2 to 10 carbons. Most of these were detected in relatively low yield. Aromatic acids were also detected, including mono- benzoic to hexabenzoic acid in all isomers, as well as small quantities of methyl-substituted aromatic acids (tentatively identified) and isomers of (carboxyphenyl~glyoxylic acids (tentatively identified). These non-chlor- ine-containing products of each acid are similar to the polybasic aromatic and aliphatic acids reported from potassium permanganate (~InO4) ox- idation (Christman et al., 1981; Liao et al., 19821. Recently de Leer et al. (1985) subjected humic acid extracted from a peat soil to aqueous chlorination under degradation-scale conditions (0.38 g humic acid per liter of solution, pH 7.2, 24-hour reaction time, ambient temperature, chlorine-to-carbon ratios of 0.39:1 and 3.35:11. The lower chlorine-to-carbon mole ratio was chosen to represent typical drinking water disinfection practice, while the higher ratio was chosen to maximize product yields. Utilizing gas chromatography/mass spectrometry (GC/MS) methods, structures were assigned to more than 100 products. The product distribution was different for the two reaction mixtures. The products detected in ether and ethyl acetate extracts of the acidified high chlorine-to-carbon ratio aqueous reaction mixture were a series of

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Chemistry and Toxicity of Disinfection 37 unchlorinated aliphatic monobasic and dibasic acids, aromatic carboxylic acids, and chlorinated aliphatic monobasic and dibasic acids, both satu- rated and unsaturated, that correspond well to those reported in the ex- periments on isolated aquatic humic and fulvic acids (Tables 3-1 and 3-21. The predominant chlorinated compounds were DCA, TCA, and 2,2- dichlorobutanedioic acid (c~,~-dichlorosuccinic acid), also in agreement with the earlier findings. Aqueous chlorination of humic acid derived from soil at a high chlorine- to-carbon ratio (3.35:1) produced two new classes of compounds (Figure 3-3) (de Leer et al., 1985~. These were the cyano-substituted alphatic monobasic acids, 3-cyanopropanoic acid and 4-cyanobutanoic acid, and the chlorinated aromatic carboxylic acids, 4-chlorobenzoic acid, 2-chlo- robenzoic acid, 2-chlorophenylacetic acid, 4-chlorophenylacetic acid, 2,6- dichlorophenylacetic acid, and 2,4-dichlorophenylacetic acid. This con- stituted the first definitive report of the production of chlorinated aromatic compounds from the aqueous chlorination of humic material. De Leer and coworkers (1985) found that a greater number of com- pounds with higher boiling points were formed at the lower chlorine-to- carbon ratio than at the higher ratio, although the classes of compounds formed were similar. Also produced at the lower ratio was a group of compounds termed "chlorofo~ precursors" because they contained a trichloromethyl group adjacent to a group susceptible to further oxidation. These structures, described above, may be divided into two groups: one with the trichloromethyl group next to a hydroxyl group and the other with the trichloromethyl group next to a carbonyl group conjugated with a carbon-to-carbon double bond (Figure 3-31. Holmbom et al. ~ 1 98 1 , 1 984) discovered a series of acids, the furanones, in chlorinated kraft pulp waste. Recently, Hemming and colleagues (1986) showed that low concentrations (~g/liter) of these compounds were formed when aqueous humic and drinking water samples were chlorinated at 1: 1 chlorine-to-carbon weight ratios at pH 7. After chlorination, these non- volatile compounds were concentrated and separated by high-pressure liquid chromatography (HPLC). Almost all of the mutagenic activity in- jected by chlorination was found to be in a relatively narrow HPLC frac- tion. After methylation by CI and EI mass spectrometry, the major contributor was tentatively identified as 3-chloro-4-(dichloromethyl)-5-hydroxy-2~5H)- furanone. This same compound was also found by Meier et al. (1986~. A number of studies have been conducted with commercial materials of unknown origin sold as humic acid (Bull et al., 1982; Coleman et al., 1984; Meier et al., 1983; Seeger et al., 1985~. These materials appear to be European lignitic coal extract rather than soil or aquatic humic acid (Malcolm and MacCarthy, 1986~. Chlorination products included chlo- roacetonitriles, chloroketones, and chlorobenzenes (Coleman et al., 19841.

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Chemistry and Toxicity of Disinfection 69 Becke, C., D. Mater, and H. Sontheimer. 1984. Origin of trichloronitromethane in drinking water. Vom Wasser 62:125-135. (in German; English summary) Bieber, T. I., and M. L. Trehy. 1983. Dihaloacetonitriles in chlorinated natural waters. Pp. 85-96 in R. L. Jolley, W. A. Brungs, J. A. Cotruvo, R. B. Cumming, J. S. Mattice, and V. A. Jacobs, eds. Water Chlorination: Environmental Impact and Health Effects. Vol. 4. Book 1: Chemistry and Water Treatment. Ann Arbor Science, Ann Arbor, Mich. Boyce, S. D., and J. F. Hornig. 1983. Reaction pathways of trihalomethane formation from the halogenation of dihydroxyaromatic model compounds for humic acid. Environ. Sci. Technol. 17:202-211. Bray, W. 1906. Beverage zur Kenntnis der Halogensauerstoffverbindungen. Abhandlung III. Zur Kenntnis des Chlordioxyds. Z. Phys. Chem. 54:569-608. Brenniman, G. R., J. Vasilomanolakis-Lagos, J. Amsel, T. Namekata, and A. H. Wolff. 1980. Case-control study of cancer deaths in Illinois communities served by chlorinated or nonchlorinated water. Pp. 1043-1057 in R. L. Jolley, W. A. Brungs, R. B. Cumming, and V. A. Jacobs, eds. Water Chlorination: Environmental Impact and Health Effects, Vol. 3. Ann Arbor Science, Ann Arbor, Mich. Bull, R. J., M. Robinson, J. R. Meier, and J. Stober. 1982. Use of biological assay systems to assess the relative carcinogenic hazards of disinfection by-products. Environ. Health Perspect. 46:215-227. Calabrese, E. J. 1984. Ecogenetics: Genetic variation in susceptibility to environmental agents. John Wiley, New York. 341 pp. Calabrese, E. J., H. M. Horton, and D. A. Leonard. In press. The effects of dehydro- epiandrosterone and ethanol on acetylephenylhydrazine-stressed human erythrocytes. J. Environ. Sci. Health. Cantor, K. P. 1982. Epidemiological evidence of carcinogenicity of chlorinated organics in drinking water. Environ. Health Perspect. 46:187-195. Cantor, K. P., R. Hoover, P. Hartge, T. J. Mason, D. T. Silverman, and L. I. Levin. 1985. Drinking water source and risk of bladder cancer: A case-control study. Pp. 145- 152 in R. L. Jolley, R. J. Bull, W. P. Davis, S. Katz, M. H. Roberts, Jr., and V. A. Jacobs, eds. Water Chlorination: Chemistry, Environmental Impact and Health Effects, Vol. 5. Lewis Publishers, Chelsea, Mich. Carlo, G. L., and C. J. Mettlin. 1980. Cancer incidence and trihalomethane concentrations in a public drinking water system. Am. J. Public Health 70:523-525. Cheh, A. M., J. Skochdopole, C. Heilig, P. M. Koski, and L. Cole. 1980a. Destruction of direct-acting mutagens in drinking water by nucleophiles: Implications for mutagen identification and mutagen elimination from drinking water. Pp. 803-815 in R. L. Jolley, W. A. Brungs, R. B. Cumming, and V. A. Jacobs, eds. Water Chlorination: Environ mental Impact and Health Effects, Vol. 3. Ann Arbor Science, Ann Arbor, Mich. Cheh, A. M., J. Skochdopole, P. Koski, and L. Cole. 1980b. Nonvolatile mutagens in drinking water: Production by chlorination and destruction by sulfite. Science 207:90-92. Cheh, A. M., R. E. Carlson, J. R. Hildebrandt, C. Woodward, and M. A. Pereira. 1983. Contamination of purified water by mutagenic electrophiles. Pp. 1221-1235 in R. L. Jolley, W. A. Brungs, J. A. Cotruvo, R. B. Cumming, J. S. Mattice, and V. A. Jacobs, eds. Water Chlorination: Environmental Impact and Health Effects, Vol. 4. Book 2: Environment, Health, and Risk. Ann Arbor Science, Ann Arbor, Mich. Christman, R. F., J. D. Johnson, J. R. Hass, F. K. Pfaender, W. T. Liao, D. L. Norwood, and H. J. Alexander. 1978. Natural and model aquatic humics: Reactions with chlorine. Pp. 15-28 in R. L. Jolley, H. Gorchev, and D. H. Hamilton, Jr., eds. Water Chlorination: Environmental Impact and Health Effects, Vol. 2. Ann Arbor Science, Ann Arbor, Mich.

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70 OR ~ N K' NG WATER AN D ~ EALTH Christman, R. F., J. D. Johnson, F. K. Pfaender, D. L. Norwood, M. R. Webb, J. R. Hass, and M. J. Bobenrieth. 1980. Chemical identification of aquatic humic chlorination products. Pp. 75-83 in R. L. Jolley, W. A. Brungs, R. B. Cumming, and V. A. Jacobs, eds. Water Chlorination: Environmental Impact and Health Effects, Vol. 3. Ann Arbor Science, Ann Arbor, Mich. Christman, R. F., W. T. Liao, D. S. Millington, and J. D. Johnson. 1981. Oxidative degradation of aquatic humic material. Pp. 979-999 in L. H. Keith, ed. Advances in the Identification & Analysis of Organic Pollutants in Water, Vol. 2. Ann Arbor Science, Ann Arbor, Mich. Christman, R. F., D. L. Norwood, D. S. Millington, J. D. Johnson, and A. A. Stevens. 1983. Identity and yields of major halogenated products of aquatic fulvic acid chlori- nation. Environ. Sci. Technol. 17:625-628. Coleman, W. E., J. W. Munch, W. H. Kaylor, R. P. Streicher, H. P. Ringhand, and J. R. Meter. 1984. Gas chromatography/mass spectroscopy analysis of mutagenic extracts of aqueous chlorinated humic acid. A comparison of the byproducts to drinking water contaminants. Environ. Sci. Technol. 18:674-681. Condie, L. W., R. D. Laurie, and J. P. Bercz. 1985. Subchronic toxicology of humic acid following chlorination in the rat. J. Toxicol. Environ. Health 15:305-314. Cooper, W. J., M. F. Mehran, R. A. Slifker, D. A. Smith, J. T. Villate, and P. H. Gibbs. 1982. Comparison of several instrumental methods for determining chlorine residuals in water. J. Am. Water Works Assoc. 74:546-552. Cragle, D. L., C. M. Shy, R. J. Struba, and E. J. Siff. 1985. A case-control study of colon cancer and water chlorination in North Carolina. Pp. 153-159 in R. L. Jolley, R. J. Bull, W. P. Davis, S. Katz, M. H. Roberts, Jr., and V. A. Jacobs, eds. Water Chlorination: Chemistry, Environmental Impact and Health Effects, Vol. 5. Lewis Pub- lishers, Chelsea, Mich. Crump, K. S. 1983. Chlorinated drinking water and cancer: The strength of the epide- miologic evidence. Pp. 1481-1491 in R. L. Jolley, W. A. Brungs, J. A. Cotruvo, R. B . Cumming, J. S. Mattice, and V. A. Jacobs, eds. Water Chlorination: Environmental Impact and Health Effects, Vol. 4. Book 2: Environment, Health, and Risk. Ann Arbor Science, Ann Arbor, Mich. Crump, K. S., and H. A. Guess. 1982. Drinking water and cancer: Review of recent epidemiological finding and assessment of risks. Annul Rev. Public Health 3:339-357. Cumming, R. B., R. L. Jolley, N. E. Lee, L. R. Lewis, J. E. Thompson, and C. I. Mashni. 1983. Mutagenicity of nonvolatile organics in undis~nfected and disinfected wastewater effluents. Pp. 1279-1309 in R. L. Jolley, W. A. Brungs, J. A. Cotruvo, R. B. Cumming, J. S. Mattice, and V. A. Jacobs, eds. Water Chlorination: Environmental Impact and Health Effects, Vol. 4. Book 2: Environment, Health, and Risk. Ann Arbor Science, Ann Arbor, Mich. Dakin, H. D. 1916. The oxidation of amino-acids to cyanides. Biochem. J. 10:319-323. de Greef, E., J. C. Morris, C. F. van Kreijl, and C. F. H. Morra. 1980. Health effects in the chemical oxidation of polluted waters. Pp. 913-924 in R. L. Jolley, W. A. Brungs, R. B. Cumming, and V. A. Jacobs, eds. Water Chlorination: Environmental Impact and Health Effects, Vol. 3. Ann Arbor Science, Ann Arbor, Mich. de Leer, E. W. B., and C. Erkelens. 1985. Chloroform Production from Model Compounds of Aquatic Humic Material. The Role of Pentachlororesorcinol as an Intermediate. Paper presented at the International Symposium on Organic Micropollutants in Drinking Water and Health, Amsterdam, The Netherlands.

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